Large scale production of catalyst-free poly(ethylene succinate) with intrinsic antibacterial property through the design of hyperthermostable quaternary ammonium monomers

Zhang, Hongjie; Fang, Tianxiang; Yao, Xuxia; Zhu, Weipu

doi:10.1016/j.cej.2022.135949

Cited by 10 publications

(10 citation statements)

References 53 publications

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“…An amphiphilic alternative multiblock copolymer, poly[oligo (ethylene glycol) mercaptosuccinate-co-butylene mercaptosuccinate] (POEGBMS), containing a hydrophilic OEG block and a hydrophobic poly(butylene mercaptosuccinate) block with multiple thiol groups, was synthesized from oligo(ethylene glycol), 1,4-butanediol and mercaptosuccinic acid through direct melt polycondensation, which is suitable for large scale synthesis of functional polyesters. [36][37][38][39] POEGBMS can co-selfassemble with AD-DOX and CD-acryl into micelles in aqueous solution. The AD moiety in AD-DOX served as the guest to insert into the inner hydrophobic cavity of CD, and CD-acryl not only provided the host CD moiety, but also served as the crosslinker for POEGBMS micelles.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular polymeric prodrug micelles for efficient anticancer drug delivery

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Supramolecular polymeric prodrug micelles for efficient anticancer drug delivery

et al. 2022

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“…Being endowed with specific functionality like proper antibacterial property will further widen the potential application fields of next-generation biobased barrier polymer materials. , It will be a significant advance if polyesters without additional antibacterial agents show certain intrinsically antibacterial properties. Antibacterial properties of the synthesized polyesters were investigated against Corynebacterium glutamicum and Escherichia coli by bacterial adsorption measurement and an inhibition zone test.…”

Section: Resultsmentioning

confidence: 99%

Effects of Different Isomers of Thiophenedicarboxylic Acids on the Synthesis and Properties of Thiophene-Based Sustainable Polyesters

Tian

Wang

et al. 2023

ACS Sustainable Chem. Eng.

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The need for high-performance bioplastics brings new challenges to the design and preparation of next-generation sustainable bioplastics. With the emergence of a number of biobased monomers with a similar chemical structure in recent years, it is necessary to conduct a systematic and in-depth study on the effects of different isomers of monomers on the final material properties. Considering the potential barrier and bacteriostatic properties of emerging thiophene-based polyesters, this work systematically investigated the effects of different isomers of thiophenedicarboxylic acids (TFDCAs), 2,5-TFDCA and 3,4-TFDCA, on the synthesis and properties of polyesters by a combination of experiments and molecular simulations. A novel biobased polyester based on the 3,4-TFDCA isomer was synthesized and compared with its analogue. Theoretical studies modeled through population balances were performed to simulate the polymerization kinetics of these two polyesters. Contrary to expectations, we successfully prepared high-molecular-weight poly(1,4-butylene 3,4-thiophenedicarboxylate) (3,4-P14BTF) via melt polycondensation. As we know, for the polyesters based on the analogous phthalic acid, high molecular weights cannot be obtained by this strategy. Barrier properties were further systematically studied from both theoretical calculation and experimental perspectives. The superior gas and water vapor barrier properties of semicrystalline poly(1,4-butylene 2,5-thiophenedicarboxylate) (2,5-P14BTF) could be attributed to the decreased chain mobility and smaller fractional free volume. More intriguingly, they exhibited improved bacteriostatic effect compared to poly(lactic acid) (PLA), while no notable difference was observed between 2,5-and 3,4-isomers. 3,4-P14BTF could be degraded under milder conditions than 2,5-P14BTF enabled by methanolysis with the imidazole acetate ionic liquid catalyst. Therefore, in-depth analysis of the effects of different isomers of monomers should be considered for the design and preparation of new high-barrier and antibacterial polymeric materials for advanced applications such as biobased active food packaging and electronic encapsulation.

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“…Indeed, our previous work showed that [C16][SIPA], which contains a benzene and an imidazole ring, exhibits a high thermal stability with a decomposition temperature of 361 °C. [14] However, the properties of monomers based on different alkyl chain lengths were not examined, and thus to determine the optimal composition, a range of monomers containing different alkyl chains were synthesized (Figure 2A). The obtained products ([C8-C16][SIPA], QACs' anion is 5-sulfoisophthalate) and their precursors ([C8-C16][Br], QACs' anion is bromine), which were obtained in high yields, were initially characterized by 1 H nuclear magnetic resonance (NMR) spectroscopy.…”

Section: Preparation and Characterization Of The Antibacterial Monomersmentioning

confidence: 99%

“…Notably, we previously reported an environmentally friendly method for the synthesis of hyperthermostable organic antibacterial monomers bearing a diaromatic ring. This was achieved using an easily accessible imidazolium salt in combination with sodium 5-sulfoisophthalate, [14] followed by the in situ preparation of antibacterial poly(ethylene succinate)s via a catalystfree melt polycondensation approach, wherein the highly thermostable 1-hexadecyl-3-methylimidazolium 5-sulfoisophthalate ([C16][SIPA]) was used as an antibacterial comonomer.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Amounts of an Antibacterial Monomer Enable the Upcycling of Poly(Ethylene Terephthalate) Waste

et al. 2023

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Poly(ethylene terephthalate) (PET) is an important polymer with an annual output second only to polyethylene. The development of PET recycling technologies is therefore necessary to not only eliminate the harm associated with white pollution and microplastics, but also to reduce carbon emissions. Antibacterial PET, one of the most high‐value advanced materials, has improved the ability to treat bacterial infections. However, current methods of manufacturing commercial antibacterial PET require blending with an excess of metal‐based antibacterial agents, which leads to biotoxicity and a nonpersistent antibacterial activity. In addition, high‐efficiency organic antibacterial agents have yet to be employed in antibacterial PET due to their poor thermal stabilities. Herein, a solid‐state reaction for the upcycling of PET waste using a novel hyperthermostable antibacterial monomer is described. This reaction is catalyzed by the residual catalyst present in the PET waste. It is found that a catalytic amount of the antibacterial monomer enabled the low‐cost upcycling of PET waste to produce high‐value recycled PET with a strong and persistent antibacterial activity, as well as similar thermal properties to the virgin PET. This work provides a feasible and economic strategy for the large‐scale upcycling of PET waste and exhibits potential for application in the polymer industry.

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Large scale production of catalyst-free poly(ethylene succinate) with intrinsic antibacterial property through the design of hyperthermostable quaternary ammonium monomers

Cited by 10 publications

References 53 publications

Supramolecular polymeric prodrug micelles for efficient anticancer drug delivery

Supramolecular polymeric prodrug micelles for efficient anticancer drug delivery

Effects of Different Isomers of Thiophenedicarboxylic Acids on the Synthesis and Properties of Thiophene-Based Sustainable Polyesters

Catalytic Amounts of an Antibacterial Monomer Enable the Upcycling of Poly(Ethylene Terephthalate) Waste

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